ArticleNature communications2017
Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines.
Article in Nature communications, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Enabling Fluoroalkyl-Sulfonylalkylation and Fluoroalkyl-Halogenation of Alkenes and Alkynes via Photoredox Catalysis.Journal of the American Chemical Society · 2026Article
- Three-Component Radical Cross-Coupling: Asymmetric Vicinal Sulfonyl-Esterification of Alkenes Involving Sulfur Dioxide.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Recent Advances in the Enantioselective Radical Reactions.Molecules (Basel, Switzerland) · 2023Review
- Remote Radical Desaturation of Unactivated C-H Bonds in Amides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes.Molecules (Basel, Switzerland) · 2021Review
- Photo-induced copper-catalyzed alkynylation and amination of remote unactivated C(spChemical science · 2021Article
- Desaturation via Redox-Neutral Hydrogen Transfer Process: Synthesis of 2-Allyl Anilines, Mechanism and Applications.iScience · 2020Article
- Saturated oxygen and nitrogen heterocyclesChemical science · 2019Article
- Photocatalytic enantioselective α-aminoalkylation of acyclic imine derivatives by a chiral copper catalyst.Nature communications · 2019Article
- Electrochemical fluoromethylation triggered lactonizations of alkenes under semi-aqueous conditions.Chemical science · 2019Article
- Catalytic Radical Process for Enantioselective Amination of C(spAngewandte Chemie (International ed. in English) · 2018Article
- Metal-free alkene oxy- and amino-perfluoroalkylationsChemical science · 2018Article
- Rhodium-Catalyzed Enantioselective Radical Addition of CXAngewandte Chemie (International ed. in English) · 2017Article
- CFBeilstein journal of organic chemistry · 2017Article
Corrections and comments
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Although great success has been achieved in asymmetric fluoroalkylation reactions via nucleophilic or electrophilic processes, the development of asymmetric radical versions of this type of reactions remains a formidable challenge because of the involvement of highly reactive radical species. Here we report a catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes with commercially available fluoroalkylsulfonyl chlorides as the radical sources, providing a versatile platform to access four types of enantioenriched α-tertiary pyrrolidines bearing β-perfluorobutanyl, trifluoromethyl, difluoroacetyl and even difluoromethyl groups in excellent yields and with excellent enantioselectivity. The key to success is not only the introduction of the CuBr/chiral phosphoric acid dual-catalytic system but also the use of silver carbonate to suppress strong background and side hydroamination reactions caused by a stoichiometric amount of the in situ generated HCl. Broad substrate scope, excellent functional group tolerance and versatile functionalization of the products make this approach very practical and attractive.
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